1-((-)N-cyclobutylmethylmorphinan-3-yl)-N-tert-butyloxycarbonyl-β-alanine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 1-((-)N-cyclobutylmethylmorphinan-3-yl)-N-tert-butyloxycarbonyl-β-alanine
• 英文别名: MCL 438；[(1R,9R,10R)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl] 3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• 化学式: C₂₉H₄₂N₂O₄
• 分子量: 482.663
• InChiKey: ZUKHFLXNSQMMAV-ZLZBJJAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-((-)N-cyclobutylmethylmorphinan-3-yl)-N-tert-butyloxycarbonyl-β-alanine 、 三氟乙酸 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以80%的产率得到
  参考文献：
  名称：

  New Opioid Designed Multiple Ligand from Dmt-Tic and Morphinan Pharmacophores

  摘要：

  Here, we report the synthesis of a designed multi-pharmacophore ligand derived from the linkage of a delta selective peptide antagonist (Dmt-Tic) and a mu/kappa morphinan agonist butorphan (MCL 101) through a two methylene spacer. The new compound MCL 450 maintains the same characteristics as those the two reference compounds. MCL 450 represents a useful starting point for the synthesis of other multiple opioid ligands endowed with analgesic properties with low tolerance and dependence.

  DOI：

  10.1021/jm0605785
• 作为产物：
  描述：

  Boc-beta-丙氨酸 、 butorphan 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到1-((-)N-cyclobutylmethylmorphinan-3-yl)-N-tert-butyloxycarbonyl-β-alanine
  参考文献：
  名称：

  New Opioid Designed Multiple Ligand from Dmt-Tic and Morphinan Pharmacophores

  摘要：

  Here, we report the synthesis of a designed multi-pharmacophore ligand derived from the linkage of a delta selective peptide antagonist (Dmt-Tic) and a mu/kappa morphinan agonist butorphan (MCL 101) through a two methylene spacer. The new compound MCL 450 maintains the same characteristics as those the two reference compounds. MCL 450 represents a useful starting point for the synthesis of other multiple opioid ligands endowed with analgesic properties with low tolerance and dependence.

  DOI：

  10.1021/jm0605785

文献信息

• New Opioid Designed Multiple Ligand from Dmt-Tic and Morphinan Pharmacophores
  作者：John L. Neumeyer、Xuemei Peng、Brian I. Knapp、Jean M. Bidlack、Lawrence H. Lazarus、Severo Salvadori、Claudio Trapella、Gianfranco Balboni

  DOI：10.1021/jm0605785

  日期：2006.9.1

  Here, we report the synthesis of a designed multi-pharmacophore ligand derived from the linkage of a delta selective peptide antagonist (Dmt-Tic) and a mu/kappa morphinan agonist butorphan (MCL 101) through a two methylene spacer. The new compound MCL 450 maintains the same characteristics as those the two reference compounds. MCL 450 represents a useful starting point for the synthesis of other multiple opioid ligands endowed with analgesic properties with low tolerance and dependence.